Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2017-08, Vol.80 (8), p.2224-2231
• Main Authors: Waterman, Melinda J, Nugraha, Ari S, Hendra, Rudi, Ball, Graham E, Robinson, Sharon A, Keller, Paul A
• Format: Article
• Language: English
• Subjects: Antarctic Regions; Antioxidants - chemistry; Antioxidants - pharmacology; Australia; Biflavonoids - chemistry; Biflavonoids - isolation & purification; Biflavonoids - pharmacology; Bryophyta - chemistry; Bryopsida - chemistry; Coumaric Acids - chemistry; Molecular Structure; Phenols - blood; Propionates; Ultraviolet Rays
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.7b00085

Ceratodon purpureus is a cosmopolitan moss that survives some of the harshest places on Earth: from frozen Antarctica to hot South Australian deserts. In a study on the survival mechanisms of the species, nine compounds were isolated from Australian and Antarctic C. purpureus. This included five biflavonoids, with complete structural elucidation of 1 and 2 reported here for the first time, as well as an additional four known phenolic compounds. Dispersion-corrected DFT calculations suggested a rotational barrier, leading to atropisomerism, resulting in the presence of diastereomers for compound 2. All isolates absorbed strongly in the ultraviolet (UV) spectrum, e.g., biflavone 1 (UV-A, 315–400 nm), which displayed the strongest radical-scavenging activity, 13% more efficient than the standard rutin; p-coumaric acid and trans-ferulic acid showed the highest UV-B (280–315 nm) absorption. The more complex and abundant 1 and 2 presumably have dual roles as both UV-screening and antioxidant compounds. They are strongly bound to Antarctic moss cell walls as well as located inside the cells of moss from both locations. The combined high stability and photoprotective abilities of these isolates may account for the known resilience of this species to UV-B radiation and its survival in some of the toughest locations in the world.